N-(4-aminophenyl)-2-(2-nitrophenyl)acetamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(4-aminophenyl)-2-(2-nitrophenyl)acetamide
• 化学式: C₁₄H₁₃N₃O₃
• 分子量: 271.276
• InChiKey: XWIFSXNZYCHHSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(4-aminophenyl)-2-(2-nitrophenyl)acetamide 在 咪唑 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 生成 N-(4-(bis(2-((tert-butyldimethylsilyl)oxy)ethyl)amino)phenyl)-2-(2-nitrophenyl)acetamide
  参考文献：
  名称：

  Prototyping kinase inhibitor-cytotoxin anticancer mutual prodrugs activated by tumour hypoxia: A chemical proof of concept study

  摘要：

  Amide- and ester-linked kinase inhibitor-cytotoxin conjugates were rationally designed and synthesised as prototype hypoxia-activated anticancer mutual prodrugs. Chemical reduction of an aryl nitro trigger moiety was shown to initiate a spontaneous cyclisation/fragmentation reaction that simultaneously released the kinase inhibitor semaxanib (SU5416) and the amine- or alcohol-linked cytotoxin from the prodrugs. Preliminary cell testing and reduction potential measurements support optimisation of the compounds towards tumour-selective mutual prodrugs.

  DOI：

  10.1016/j.bmcl.2019.03.015
• 作为产物：
  描述：

  2-硝基苯乙酸 、 对苯二胺 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以12.11 g的产率得到N-(4-aminophenyl)-2-(2-nitrophenyl)acetamide
  参考文献：
  名称：

  Prototyping kinase inhibitor-cytotoxin anticancer mutual prodrugs activated by tumour hypoxia: A chemical proof of concept study

  摘要：

  Amide- and ester-linked kinase inhibitor-cytotoxin conjugates were rationally designed and synthesised as prototype hypoxia-activated anticancer mutual prodrugs. Chemical reduction of an aryl nitro trigger moiety was shown to initiate a spontaneous cyclisation/fragmentation reaction that simultaneously released the kinase inhibitor semaxanib (SU5416) and the amine- or alcohol-linked cytotoxin from the prodrugs. Preliminary cell testing and reduction potential measurements support optimisation of the compounds towards tumour-selective mutual prodrugs.

  DOI：

  10.1016/j.bmcl.2019.03.015

文献信息

• Prototyping kinase inhibitor-cytotoxin anticancer mutual prodrugs activated by tumour hypoxia: A chemical proof of concept study
  作者：Geraud N. Sansom、Nicholas S. Kirk、Christopher P. Guise、Robert F. Anderson、Jeff B. Smaill、Adam V. Patterson、Michael J. Kelso

  DOI：10.1016/j.bmcl.2019.03.015

  日期：2019.5

  Amide- and ester-linked kinase inhibitor-cytotoxin conjugates were rationally designed and synthesised as prototype hypoxia-activated anticancer mutual prodrugs. Chemical reduction of an aryl nitro trigger moiety was shown to initiate a spontaneous cyclisation/fragmentation reaction that simultaneously released the kinase inhibitor semaxanib (SU5416) and the amine- or alcohol-linked cytotoxin from the prodrugs. Preliminary cell testing and reduction potential measurements support optimisation of the compounds towards tumour-selective mutual prodrugs.